Solutions_Manual_for_Organic_Chemistry_6th_Ed 165

Solutions_Manual_for_Organic_Chemistry_6th_Ed 165 - 7-55...

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Unformatted text preview: 7-55 continued with rearrangement-alkyl shift-ring expansion ��H2 H C "....-A H2 -�. .� � ("�-H�. O[ H H2C-C-H H20: I H H on 2° carbocation 5-membered ring­ HOORAY! H ('xCH/'RiI .. MAJOR t -H 0 2 1° carbocation-terrible!-will rearrange; can't do hydride shift, must do alkyl shift ring expansion = a gives bridgehead Hbstraction of adjacent alkene-violates Bredfs Rule t hydride shift this is an unstable carbocation even though it is 3°; bridgehead carbons cannot be sp 2 (planar-try to make a model), so this carbocation does a hydride shift to 2°, more stable carbocation a this 2° carbocation loses an adjacent H to form an alkene; can't form at bridgehead (Bredt's Rule)­ only one other choice 158 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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